Abstract:Complex polycycles made simple: A practical synthesis of the simplest cross‐conjugated pentaene, [5]dendralene, is reported. The hydrocarbon undergoes controllable and atom‐efficient domino sequences (see scheme) to generate complex polycyclic frameworks in an operationally simple manner.
“…Aside from the classical synthesis of different dendralenes,2, 3f,j, 4a,e,f,h various metal‐catalyzed processes for dendralene synthesis have been published 2. 3a,g, 4c,d,g, 5…”
Ruthenium-catalyzed cascade transformations for the synthesis of 2,3-cyclo[3]dendralenes and multicomponent processes based thereon to generate complex polycycles are presented. The combination of allylation-cyclization sequences with diene-transmissive Diels-Alder reactions allows the rapid and selective construction of natural-product-like motifs from easily accessible starting materials in a one-pot process and provides a new method to access potential drug candidates.
“…Aside from the classical synthesis of different dendralenes,2, 3f,j, 4a,e,f,h various metal‐catalyzed processes for dendralene synthesis have been published 2. 3a,g, 4c,d,g, 5…”
Ruthenium-catalyzed cascade transformations for the synthesis of 2,3-cyclo[3]dendralenes and multicomponent processes based thereon to generate complex polycycles are presented. The combination of allylation-cyclization sequences with diene-transmissive Diels-Alder reactions allows the rapid and selective construction of natural-product-like motifs from easily accessible starting materials in a one-pot process and provides a new method to access potential drug candidates.
“…Neben der klassischen Synthese unterschiedlicher Dendralene2, 3f,j, 4a,e,f,h wurden verschiedene metallkatalysierte Verfahren zur Dendralensynthese publiziert 2. 3a,g, 4c,d,g, 5…”
Oxadisilole‐fused 9‐aminoacridines and 12‐aminobenzo[b]acridines have been synthesized by the nucleophilic addition and 1,5‐hydrogen shift reaction of arynes with 2‐aminobenzonitriles in good yield at room temperature. Dioxatrisilole‐fused 9‐aminoacridines have also been obtained. The photophysical, redox, and thermal properties of these compounds have been determined. The oxadisilole‐fused 9‐aminoacridines show potential for use as blue emitters for OLED applications, because of their high fluorescence quantum yields and good thermal stabilities. The proposed mechanism was also studied. Theoretical calculations on the HOMO and LUMO values of these compounds were performned.
“…162 Under controlled conditions, Diels−Alder dimerization of 288 led to 289 as a minor component of the reaction mixture. Upon heating in refluxing chlorobenzene, 289 underwent a remarkable domino 6π-electrocyclization/intramolecular Diels−Alder sequence to form the product 290 in good yield.…”
Section: Cycloadditions Electrocyclizations and Cycloisomerizationsmentioning
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